Month: June 2021

Synthetic Route of 55289-36-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 55289-36-6 as follows.

A mixture of 3-bromo-2-methylaniline (10 mL, 60.52 mmol), chloral hydrate (14.86 g, 89.86 mmol) and anhydrous Na2S04 (94.56 g, 665.74 mmol) in hydrochloric acid (6.4 mL, 21 1.24 mmol) and H2O (700 mL) was stirred vigorously at room temperature overnight. To the resulting mixture, hydroxylamine hydrochloride (5.86 g, 84.26 mmol) was added and the mixture was heated to reflux overnight. The reaction mixture was ice cooled, and the resulting precipitate was collected by vacuum filtration and washed copiously with H2O and dried under suction. The precipitate was re-dissolved in EtOAc (-500 mL) and washed with H2O (300 mL) and brine (300 mL) then dried over MgS04. The resulting filtrate was removed in vacuo to give 6-bromo-7-methyl-indoline-2,3-dione as a dark brown solid in quantitative yield, which was used directly in the next step without further purification. LC-MS 238.5/240.5 [M+H]+; RT 1.84 min

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; STOKES, Neil; (163 pag.)WO2017/46603; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2-Bromo-l,4-difluorobenzene(53.6 g, 277.74 mmol) in THF cooled to -50C was added to isopropyl magnesium chloride (2M in THF)( 133mL, 266 mmol). The reaction mixture thus obtained was warmed to 0C and stirred for lh. The reaction mixture was cooled again to -50C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200mL) was added dropwise to this reaction mixture with stirring and the stirring was continued at 0C for lh. The reaction mixture was quenched with saturated aqueous NH4C1 solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colourless liquid. 1H NMR (300MHz, CDC13) delta ppm 7.6-7.53(lH, m), 7.26-7.09(2H, m), 3.7(2H, t) 3.22- 3.14(2H, m), 2.28-2.16(2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; SASMAL, Pradip Kumar; AHMED, Shahadat; TEHIM, Ashok; PRADKAR, Vidyadhar; DATTATREYA, Prasanna M.; MAVINAHALLI, Nanjegowda Jagadeesh; WO2013/88256; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 460-00-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 460-00-4, name is 1-Bromo-4-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200-300 mesh) column.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Lei; Ji, Enhui; Liu, Ning; Dai, Bin; Synthesis; vol. 48; 5; (2016); p. 737 – 750;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2606-51-1, Application In Synthesis of 5-(Bromomethyl)benzo[d][1,3]dioxole

General procedure: A mixture of benzyl bromide (171 mg, 1 mmol), diphenyl disulfide (131 mg, 0.6 mmol), PPh3 (184 mg, 0.7 mmol), and [pmIm]Br21 (94 mg, 0.4 mmol) was stirred at 75 C for 1.5 h (TLC). The reaction mixture was extracted with Et2O, and the organic layer was washed with brine (2 × 5 mL) and dried (Na2SO4). Evaporation of solvent left the crude product which was purified by column chromatography over silica gel (hexane) to afford the pure product, benzyl phenyl sulfide (168 mg, 84%) as a colorless liquid. The remaining ionic liquid was washed with ether, dried under vacuum, and reused five times without appreciable loss of catalytic activity.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Banerjee, Subhash; Adak, Laksmikanta; Ranu, Brindaban C.; Tetrahedron Letters; vol. 53; 17; (2012); p. 2149 – 2152;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2550-36-9, These common heterocyclic compound, 2550-36-9, name is (Bromomethyl)cyclohexane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1 : To a solution of 3-bromo-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 4.39 mmol, 1 eq) and Cs2CO3 (2.86 g, 8.78 mmol, 2 eq) in DMF (20 mL) was added (bromomethyl)cyclohexane (1.55 g, 8.78 mmol, 1.22 mL, 2 eq). The mixture was stirred at 60C for 18 hour. The reaction mixture was filtered and the filtrate was concentrated. The crude mixture was purified by flash chromatography with petroleum ethenethyl acetate = 5:1 ~ 3: 1. 3-bromo-7-(cyclohexylmethyl)-6-methylimidazo[1,5-a]pyrazin-8(7H)-one (1 g, 3.02 mmol, 69% yield) was obtained. 1H NMR (CDCl3 , 400 MHz): delta 7.86 (s, 1 H), 6.80 (s, 1 H), 3.79 (6, J = 1.2 Hz, 2H), 2.29 (s, 3H), 1.75 -1.66 (m, 6H), 1.22 – 1.04 (m, 5H). LC-MS: tR = 0.791 min (method 15), m/z = 325.9 [M + H]+.

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H3BrF4

Example 26 Synthesis of TRV 1 158[00166] TRV 1158 – phenyl(4-(3-(pyrrolidin- l -yl)-4-(trifluoromethy])phenyl)piperazin- l – yl)methanone[00167] Scheme for TRV 1 158DIPEA / N P[00168] A mixture of 4-bromo-2-fluorobenzotrifluoride ( l .5 l l g, 6.2 mmol), pyrrolidine (0.62 mL, 7.46 mmol), DIPEA ( 1.6 mL, 9.33 mmol) and NMP (8 mL) were sealed in a tube and heated to 120 C overnight. The solution was cooled to room temperature and diluted with water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed successively with H2O, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2SC>4. The mixture was filtered and concentrated to give a crude oil, which was purified via flash chromatography (5 % EtOAc / hexane) to give 0.9667 g (53 % yield) of desired product. This bromo-intermediate (0.5312 g, 1.8 mmol), benzoylpiperazine hydrochloride (0.4987 g, 2.2 mmol) and NaO/Bu (0.5189 g, 5.4 mmol) were charged to a flask which was subsequently purged and evacuated with argon (3 cycles). Toluene (5.4 mL) and NMP (3.2 mL) were then added and the solution was degassed for 30 minutes before added Pd2(dba)3 (0.033 g, 0.036 mmol) and BINAP (0.045 g, 0.072 mmol) all at once. The flask was then heated to 100 C overnight under argon. The mixture was cooled to room temperature and diluted with EtOAC before filtering through Celite. The organic layer was then washed successively with H20, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2S04. The mixture was filtered and concentrated to give 0.5081 g of crude oil. The oil was purified via flash chromatography (45 % EtOAc / hexane) to give another crude oil that was slightly impure. This oil was crystallized from EtOAc (solvent) and hexane (anti-solvent) to give 0.101 g of white crystals of TRV 1158, phenyl(4-(3-(pyrrolidin-l -yl)-4- (trifluoromethyl)phenyl)piperazin- l-yl)methanone. NMR (500 MHz, DMSO) delta = 7.47-7.41 (m, 5H), 7.35 (d, J = 8.5 Hz, 1 H), 6.49 (dd, J = 8.5, 1.5 Hz, 1 H), 6.46 (m, 1 H), 3.72 (br s, 2H), 3.45 (br s, 2H), 3.30 (br s, 4H), 3.23-3.20 (m, 4H), 1.88- 1.83 (m, 4H).

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H11Br

Step 2: To a suspension of 6-(4-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one (150 mg, 456.84 micromol) in anhydrous DMF (5 ml_) was added (bromomethyl)cyclopentane (89. mg, 548.21 micromol) and K2CO3 (95 mg, 685.27 micromol). The mixture was heated at 60C for 12 h. LCMS showed 23% TM. The mixture was concentrated and the residue was dissolved in DCM (20 ml_) and H2O (20 ml_). The aqueous layer was extracted with DCM (20 ml_). The combined organics were washed with H2O (20 ml_), dried over Na2SO4, filtered, concentrated and purified by prep-TLC (DCM/MeOH=50/1 ) to give 7- (cyclopentylmethyl)-6-(4-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one (25.90 mg, 13.67% yield) . 1H NMR (CDCI3 400MHz): 5 7.17-7.13 (m, 2H), 7.1 1 -7.06 (m, 2H), 6.64 (s, 1 H), 4.13-4.10 (m, 2H), 3.94 (s, 2H), 3.90 (d, J=7.2 Hz, 2H), 3.59-3.53 (m, 2H), 3.13-3.12 (m, 1 H), 2.28-2.10 (m, 1 H), 2.19-2.16 (m, 2H), 1 .94-1 .91 (m, 2H), 1 .71 -1 .68 (m, 4H), 1 .54-1 .45 (m, 2H), 1 .33-1 .28 (m, 2H). LC-MS: tR = 2.84 min (METHOD 3), m/z = 41 1 .2 [M + H]+

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[00236] A suspension of 3 -bromo-4-methylaniline (184 mg, 1.0 mmol), 2-(tributylstannyl)- 1,3-oxazole (430 mg, 1.2 mmol), CuO (8 mg, 0.1 mmol) and Pd(PPli3)4 (1 15 mg, 0.1 mmol) in dioxane (2 mL) was stirred at 100 C for 3 hours under argon atmosphere on microwave synthesizer. The crude product was purified by prep-HPLC (MeCN/10 mM NH4HCO3) to give 4-methyl-3-(l,3-oxazol-2-yl)aniline (92 mg, 52%) as an oil. ES-MS m/z: 175.2 [M + H]+. LC- MS Purity (254 nm): > 99%; tR= 1.31 min.

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (253 pag.)WO2016/73891; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5469-19-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5469-19-2 name is 1-Bromo-2,4,5-trimethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

i 2,4,5-Trimethylbenzoic acid n-Butyllithium (100 ml of a 2.5M solution in hexanes) was added to a solution of 5-bromo-1,2,4-trimethylbenzene (50 g) in tetrahydrofuran (600 ml) at -70 C. After 1.5 hours the solution was warmed to -40 C. then cooled to -70 C. Carbon dioxide gas was bubbled through the solution for 10 minutes and the mixture was allowed to warm to room temperature. The solvent was evaporated and the residue partitioned between water and isohexane. The aqeous layer was acidified to pH 1 and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure. Yield 36.7 g. 1H NMR: delta (CDCl3) 7.85(s, 1H), 7.04(s, 1H), 2.59(s, 3H), 2.28(s, 3H), 2.27(s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,4,5-trimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca U.K. Limited; US6162808; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 61326-44-1, Product Details of 61326-44-1

Under argon protection,Tetrakis(4-bromophenyl)ethene 210.7 mg, 0.33 mmol) was added to the reaction flask in that order.3,4,5-trifluorobenzeneboronic acid (274.9 mg, 1.56 mmol),Potassium carbonate (135.4 mg, 0.98 mmol),Tetrakis(triphenylphosphine)palladium (20.3 mg, 0.018 mmol),Tetrabutylammonium bromide (12.3 mg, 0.038 mmol),Add 20 mL of toluene and 5 mL of deionized water.The mixture was heated to 100 ° C, reacted for 27 h, and the reaction was monitored by thin layer chromatography.After the system was lowered to 27 ° C, the liquid was separated.The aqueous phase was extracted with dichloromethane (15 mL×3) and the organic phases were combined.Add anhydrous sodium sulfate and filter,The filtrate is concentrated and subjected to thin layer chromatography.The developing agent ratio is dichloromethane: n-hexane (V: V) = 2:1,The bright blue band of the product (observed under a 365 nm UV lamp) is scraped off.After fully crushing, pour into a sand core funnel and rinse with 80 mL of dichloromethane.Evaporate dry solvent,Obtaining a yellow solid is the target product F-TPE,The weight was 169.2 mg, and the yield was 61.02percent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,1,2,2-Tetrakis(4-bromophenyl)ethene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Jinan; Miao Jinling; Xiong Zhixin; Nie Yong; Zhang Hao; (15 pag.)CN108947766; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary